Wendy

Wendy Wendy, where do I start?

Wendy was a cute, bit older native working girl and the one I had the most encounters with.

The first time I saw Wendy was in the mid 90s. 95 or 96. I had finished my delivery shift and was heading home at 2:30am on a summer evening. She was in her late 30s and I was still in my 20s.

I spotted her walking a couple of streets from mine. I drove around the block a couple of times to make sure no cops were around and then stopped for her.

After the usual ‘are you a cop?’ ‘No are you a cop?’

As I only had $40 on me, I couldn’t negotiate much, so when she said $40 for a blow job, I took it.

I found a dark spot in the neighborhood and parked.

Prior to Wendy, I hadn’t had much experience with hookers. All of the previous ones were cute ones and they milked everything you wanted to do. Want to touch tits while getting a blow job? $10 more. Wanna feel between the legs, $20 more, etc...

So it was a surprise to me when I handed over the money, and as I was pulling down my pants, Wendy took off her top revealing a couple of massive tits, we’re talking G or larger cup size. They were quite impressive and they didn’t sag much.

I finished pulling down my pants and as usual left them around my ankles.

“It would better if you take your pants and underwear completely off.” Wendy told me.

“Really?” It sounded dubious.

“Yes, I’ll have more room.” She replied.

So I pulled them completely off and shoved them behind me away from her. I was afraid that she may try to take my wallet.

But I had nothing to worry about.

A soon as my pants were off, Wendy said to put my right foot on the passenger seat behind her, spreading my legs to the max.

I was very surprised when she started. She didn’t go for my dick trying to get it over as quickly as possible. After I spread my legs, and not knowing what to expect, Wendy put her hands under my knees and pulled me towards her. I helped, but was surprised at how strong she was. She kept pulling until my ass rested on the right edge of the seat right next to the transmission shifter. She got down on her knees in the passenger legs well, and proceeded to rub those massive tits of hers on my legs and cock. It was erotic as hell. I had never felt my ball being tickled with a pair of hard nipples.

By the time she was ready to handle my cock directly I was harder than steel. I was so turned on by this woman.

Next thing she did was to open the condom package that appeared out of nowhere and without letting go of my cock, she ripped it apart with her teeth and a free hand and put the rubber in her mouth and rolled it onto my cock with her lips.

She was fucking amazing.

She worked my cock like the pro she was. I was ready to blow in less than a minute but she chose to prolong it.

When she finished me off, I shot a load that felt like my soul left with it.

She was awesome.

Wendy even waited for me to recover, pulled off the condom, tied it, then used a wet paper towel to clean me up. The only thing that was missing from her service was to dress me back up.

To say I was satisfied would be an understatement.

We exchanged some pleasantries and I dropped her off where I found her.

Soon I found myself looking for Wendy for a repeat.

It took over a couple of months to find her again.

The second time it was different.

She did take off her top and she did the teasing with her tits as before, but this second time, after she put the condom on my cock, she put her mouth on it too, but didn’t move. She just kept half of my cock in her mouth.

I started thinking to myself ‘what’s wrong with her this time?’.

To signal to her that she should move, I shoved my hips up, but she didn’t start moving. I had never fucked anybody’s face before, so I didn’t know what the problem was.

Out of desperation, I pushed my cock up again and she remained stationary. I figured she wanted me to fuck her mouth, which was new to me.

So I did.

I put my hands on the back of her head and started fucking up into her mouth. Wendy didn’t resist or try to stop me. However, since I never done this before, I didn’t fuck hard nor deep. I didn’t want to ruin it with this woman.

It took longer than the previous time since I was making a physical effort. But finally I shot a very nice load into the condom and she cleaned me up like before.

She didn’t leave right away this time, she sat in the car and she seemed in a chatty mood. Nothing really interesting, after all she was only a hooker but she chatted about inconsequential things for a good ten minutes before I was too tired and started driving to where I had found her.

From then on, and for about a couple of years, I would look for Wendy whenever I wanted some casual sex. Every time I found her she would do that. Over time I learned that she loved being deep throated for some reason. As she put her mouth on my cock I would push her head down all the way until her lips touch the base of my cock.

Since I didn’t shoot too quickly, by the time I did, Wendy’s spit and drool would be coating my balls, ass and car seat. So I started keeping a towel in my car for such occasions. Before she starts, I would put the towel on the seat and sit on it.

Our sessions got longer and longer. Wendy’s chats became a normal thing and sometimes she would keep chattering for hours. When that happens, I would simply drive her to her house.

One day were were talking before she fucked her face with my dick and I noted to her that we’ve never had vaginal sex. Wendy expressed surprise at that fact. So that time, after she sucked me for a good ten minutes, she asked, “Do you want to try my pussy?”

“Yes, sure.” I answered.

Wendy lay back in the seat and pulled up her skirt revealing that she was pantiless. As usual for hookers, she was hairless.

As I fucked her pussy, which was quite loose, I started playing with her clit and noticed that her pubic skin was unusually soft.

“Nice shave.” I commented as I moved in and out while rubbing her clit.

“What do you mean?”

“You’ve done a great job shaving is what I mean. Your skin is so soft I can’t feel even one hair.”

“I don’t shave.” She exclaimed indignantly then burst out laughing.

“What do you mean you don’t shave?”

“I don’t shave.”

“You don’t have any hair on your pussy?”

“I don’t have any hair anywhere except the top of my head.” Was her smug reply.

“How can that be?” All the while still fucking into her pussy and twirling her clit in circles.

“Half of us Indian women,” (yes, she referred to herself as Indian, instead of native or whatever they like to use to be politically correct), “Don’t grow any hair anywhere except our head. You didn’t know that?”

“How would I know that? I’ve never met anybody who was naturally hairless like you.”

“You don’t like it?”

“I love it. Your cunt is so soft and smooth, and a joy to fuck.”

“Glad you like it.”

It took a while for me to cum since she was loose and I was wearing a condom. I couldn’t really feel anything other that warmth. But eventually, I did.

After that encounter, Wendy would take off all her clothes every time I picked her up. Funny thing is that I never went to her place as she had an 18 year-old son, and I never took her to mine. We always did it in the front seat of my car.

One time as she chattered away after blowing me, she suddenly asked, “Bob, would you marry me?”

I was surprised to say the least. I didn’t know how to answer. On the one hand I didn’t want to upset her and on the other, there were a million reasons why this would be a bad idea.

I stayed silent for a while thinking how to let her down without upsetting her too much.

“Look Wendy, I like you a lot. I love your attitude and what you do for me. But we can’t marry. I’m younger than you and I want to have a family. You can’t give me kids (she had told me once she was sterile after having her tubes tied after giving birth to her son), and I want a big family. We also come from very different backgrounds and it wouldn’t work.”

“Bob, I understand. Really. I was hoping for a miracle, but you’re right. Forget I said anything.”

I drove her home. I expected her to be silent because of her disappointment, but her chattiness knew no bound. She chattered away as if nothing awkward had happened.

One time, it was my birthday and I told her so.

“Oh goody. I’ll give you a treat,” She said.

With that she lowered the back of the seat all the way and managed to twist around so that her feet were above the car’s back seat and her head was a little beyond the front seat’s cushion.

“Hop in here and kneel.” Wendy instructed me.

I did after taking off my pants and underwear, and as soon as I was in position Wendy took my cock in her mouth without a condom. It was the first time she did.

Her head was hanging down off the seat which straightened her mouth and throat.

“Go ahead, fuck my throat. If I need air I’ll tap you on the leg. Other than that, go ahead and fuck as much as you want.”

The idea blew my mind. Here I was offered to fuck a woman’s mouth and throat as hard as I wanted, as deep and as long as I wanted. I’ve never been offered that before.

I had a blast, but unfortunately, since it was bareback and something so amazing, I only lasted maybe three or four minutes tops.

I fucked and I fucked. I treated her mouth like I would treat a pussy, and didn’t hold back anything. Since I pulled out regularly, Wendy didn’t need to tap my leg. As I fucked her face, I played with her nipples and pussy.

I shot the biggest, most intense, load I’ve ever done directly into her throat.

After I was done, I pulled out and moved out of the passenger side well and back into the driver’s seat. Wendy turned back around and she was a site to behold. Her hair was messed up and full of spit and dirt from the car’s floor, the little make up she wore was messed up, there was liquid all over her face.

She pulled down the sunshade and looked into the mirror at herself.

“Wow, do I look pretty?” She turned to me and smiled a huge smile.

I couldn’t help but burst out laughing.

“Beautiful baby, just beautiful.” Was my reply.

Wendy used paper towels and wet towels to clean up her face, but her hair was a mess, so I drove her home as she chattered away as usual.

The time before last time I was with Wendy, I never expected to be like that.